反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A solution of 15 (497 mg, 0.64 mmol) in DMF (10 mL) was treated with sodium hydride (18.5 mg, 0.77 mmol) at 0° C. under an Ar atmosphere. After stirring at 0° C. for 30 min, benzyl 2-bromoacetate (0.15 mL, 0.96 mmol) was added. The mixture was stirred at 0° C. for another 30 min and then warmed to room temperature overnight. The solvent was evaporated to dryness and extracted with EtOAc/H2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with 40% EtOAc in Hexane (with 0.1% Et3N) to yield 453 mg (76%) of 16 as a light yellow oil. Rf=0.28 (in 40% EtOAc/hexane); 1H NMR (300 MHz, CDCl3) δ 7.32 (m, 5H), 6.96 (d, 2H, J=7.2 Hz), 6.86 (d, 1H, J=8.4 Hz), 6.72 (dd, 1H, J=7.8 and 1.5 Hz), 6.59 (m, 3H), 5.28 (s, 4H), 5.15 (s, 2H), 4.89 (s, 1H), 4.64 (s, 2H), 4.01 (s, 4H), 3.86 (m, 4H), 3.58 (m, 4H), 3.39 (s, 6H), 1.39 (s, 18H); 13C NMR (75 MHz, CDCl3) 6170.3, 168.8, 150.7, 149.9, 147.5, 146.6, 146.5, 144.4, 144.3, 139.1, 138.9, 135.3, 128.6, 128.4, 128.3, 122.9, 120.0, 117.0, 116.9, 116.2, 116.1, 115.8, 105.9, 94.7, 81.2, 71.5, 68.1, 66.7, 66.6, 59.0, 54.5, 42.6, 28.0; 19F NMR (282 MHz, CDCl3) δ −140.2 (dd, 2 F); mass spectrum, calculated for C46H55F2NO13 (M−17) 909.4, Found 910.1.
WORKUP
后处理
- stirringThe mixture was stirred at 0° C. for another 30 min
- temperaturewarmed to room temperature overnight
- customThe solvent was evaporated to dryness
- extractionextracted with EtOAc/H2O
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography
- washeluting with 40% EtOAc in Hexane (with 0.1% Et3N)